[(2R,3S,6S)-3-Acet-yloxy-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate.

In the title compound, C(18)H(19)N(3)O(5), the 3,6-dihydro-2H-pyran ring adopts a half-chair, distorted towards a half-boat, conformation with Q(T) = 0.5276(14) Å. The benzene ring is twisted out of the place of the triazole ring [dihedral angle = 23.54 (8)°]. In the crystal, supra-molecular layers in the ac plane are formed through C-H⋯O and C-H⋯π(triazole) inter-actions. These stack along the b axis being connected by C-H⋯N contacts.

Related literature

For background to the chemical attributes of C-glycosides, see: Ritchie et al. (2002 ▶); Hanessian & Lou (2000 ▶); Hultin (2005 ▶); Zou (2005 ▶). For chiral properties of C-glycosides, see: Nakata (2005 ▶); Nicolaou et al. (2008 ▶); Somsak (2001 ▶). For additional conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H19N3O5

M = 357.36

Monoclinic,

a = 4.79932 (7) Å

b = 16.6308 (2) Å

c = 10.76331 (14) Å

β = 93.225 (1)°

V = 857.73 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.86 mm−1

T = 100 K

0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual Cu at zero diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.848, T max = 0.959

5784 measured reflections

3369 independent reflections

3304 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.084

S = 1.04

3369 reflections

237 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1591 Friedel pairs

Flack parameter: −0.09 (15)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and MarvinSketch (ChemAxon, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037305/hg5093sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037305/hg5093Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037305/hg5093Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H19N3O5	F(000) = 376
Mr = 357.36	Dx = 1.384 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 4088 reflections
a = 4.79932 (7) Å	θ = 2.7–74.0°
b = 16.6308 (2) Å	µ = 0.86 mm−1
c = 10.76331 (14) Å	T = 100 K
β = 93.225 (1)°	Prism, colourless
V = 857.73 (2) Å3	0.20 × 0.10 × 0.05 mm
Z = 2

Agilent SuperNova Dual Cu at zero diffractometer with an Atlas detector	3369 independent reflections
Radiation source: fine-focus sealed tube	3304 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 4.1°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→20
Tmin = 0.848, Tmax = 0.959	l = −13→8
5784 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1259P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3369 reflections	Δρmax = 0.14 e Å−3
237 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 1591 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (15)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	−0.1199 (2)	0.49978 (6)	0.39298 (9)	0.0183 (2)
O2	0.1131 (3)	0.41952 (8)	0.69075 (13)	0.0374 (3)
O3	0.0424 (2)	0.54932 (7)	0.63709 (10)	0.0230 (2)
O4	0.0156 (3)	0.75452 (8)	0.58495 (11)	0.0298 (3)
O5	0.1489 (2)	0.70479 (7)	0.40355 (11)	0.0226 (2)
N1	0.2553 (3)	0.37406 (8)	0.10112 (11)	0.0163 (2)
N2	0.2724 (3)	0.44506 (8)	0.03950 (12)	0.0205 (3)
N3	0.1016 (3)	0.49499 (8)	0.09098 (12)	0.0202 (3)
C1	0.4329 (3)	0.30870 (9)	0.07023 (15)	0.0174 (3)
C2	0.5395 (4)	0.30667 (10)	−0.04686 (15)	0.0231 (3)
H2	0.4855	0.3461	−0.1074	0.028*
C3	0.7260 (4)	0.24640 (11)	−0.07433 (16)	0.0274 (3)
H3	0.8035	0.2451	−0.1536	0.033*
C4	0.7999 (4)	0.18788 (10)	0.01356 (17)	0.0265 (3)
H4	0.9275	0.1466	−0.0056	0.032*
C5	0.6871 (4)	0.18983 (10)	0.12911 (17)	0.0278 (4)
H5	0.7362	0.1494	0.1888	0.033*
C6	0.5023 (3)	0.25052 (10)	0.15854 (15)	0.0232 (3)
H6	0.4251	0.2520	0.2379	0.028*
C7	0.0740 (3)	0.37932 (9)	0.19199 (13)	0.0177 (3)
H7	0.0251	0.3385	0.2485	0.021*
C8	−0.0244 (3)	0.45681 (9)	0.18467 (13)	0.0160 (3)
C9	−0.2265 (3)	0.49831 (9)	0.26498 (13)	0.0176 (3)
H9	−0.4020	0.4658	0.2614	0.021*
C10	−0.3016 (3)	0.58149 (9)	0.21885 (15)	0.0192 (3)
H10	−0.4012	0.5874	0.1406	0.023*
C11	−0.2323 (3)	0.64660 (9)	0.28465 (14)	0.0200 (3)
H11	−0.2926	0.6977	0.2543	0.024*
C12	−0.0613 (3)	0.64194 (9)	0.40561 (14)	0.0193 (3)
H12	−0.1821	0.6498	0.4774	0.023*
C13	0.0863 (3)	0.56087 (9)	0.41504 (14)	0.0181 (3)
H13	0.2238	0.5577	0.3488	0.022*
C14	0.2357 (3)	0.54349 (10)	0.53946 (14)	0.0225 (3)
H14A	0.3170	0.4888	0.5388	0.027*
H14B	0.3896	0.5825	0.5550	0.027*
C15	−0.0055 (3)	0.48239 (10)	0.70412 (15)	0.0247 (3)
C16	−0.2217 (4)	0.49774 (14)	0.79520 (16)	0.0342 (4)
H16A	−0.1650	0.4725	0.8749	0.051*
H16B	−0.4003	0.4750	0.7636	0.051*
H16C	−0.2422	0.5558	0.8070	0.051*
C17	0.1610 (3)	0.75859 (9)	0.49755 (14)	0.0201 (3)
C18	0.3763 (4)	0.82174 (10)	0.47939 (18)	0.0270 (4)
H18A	0.3102	0.8734	0.5100	0.041*
H18B	0.4096	0.8263	0.3907	0.041*
H18C	0.5505	0.8069	0.5256	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0217 (5)	0.0174 (5)	0.0160 (5)	−0.0037 (4)	0.0037 (4)	−0.0012 (4)
O2	0.0421 (8)	0.0277 (7)	0.0423 (8)	−0.0015 (6)	0.0020 (6)	0.0073 (6)
O3	0.0284 (6)	0.0250 (6)	0.0162 (5)	−0.0015 (5)	0.0055 (4)	−0.0001 (4)
O4	0.0357 (7)	0.0314 (7)	0.0232 (6)	−0.0047 (5)	0.0090 (5)	−0.0096 (5)
O5	0.0253 (6)	0.0199 (5)	0.0236 (6)	−0.0061 (4)	0.0104 (5)	−0.0069 (4)
N1	0.0186 (6)	0.0138 (6)	0.0165 (6)	−0.0001 (5)	0.0014 (5)	0.0012 (5)
N2	0.0269 (7)	0.0157 (6)	0.0193 (6)	0.0015 (5)	0.0053 (5)	0.0025 (5)
N3	0.0234 (6)	0.0184 (6)	0.0194 (6)	0.0005 (5)	0.0055 (5)	0.0002 (5)
C1	0.0170 (7)	0.0150 (6)	0.0203 (7)	−0.0005 (6)	0.0013 (5)	−0.0042 (6)
C2	0.0259 (8)	0.0236 (7)	0.0201 (8)	0.0013 (6)	0.0037 (6)	−0.0024 (6)
C3	0.0283 (8)	0.0291 (9)	0.0253 (8)	0.0004 (7)	0.0064 (6)	−0.0080 (7)
C4	0.0239 (8)	0.0201 (8)	0.0355 (9)	0.0033 (6)	0.0016 (7)	−0.0088 (7)
C5	0.0312 (9)	0.0201 (8)	0.0319 (9)	0.0042 (7)	−0.0014 (7)	0.0011 (7)
C6	0.0266 (8)	0.0203 (7)	0.0228 (7)	0.0027 (7)	0.0027 (6)	0.0007 (6)
C7	0.0182 (7)	0.0176 (7)	0.0174 (7)	−0.0019 (6)	0.0029 (5)	0.0005 (6)
C8	0.0162 (7)	0.0162 (7)	0.0156 (7)	−0.0027 (5)	0.0010 (5)	−0.0019 (5)
C9	0.0172 (7)	0.0180 (7)	0.0177 (7)	−0.0022 (6)	0.0025 (5)	−0.0017 (6)
C10	0.0161 (7)	0.0209 (8)	0.0210 (7)	0.0008 (5)	0.0033 (5)	0.0009 (6)
C11	0.0189 (7)	0.0186 (7)	0.0233 (8)	0.0015 (6)	0.0074 (6)	0.0012 (6)
C12	0.0195 (7)	0.0173 (7)	0.0219 (8)	−0.0037 (6)	0.0078 (6)	−0.0030 (6)
C13	0.0180 (7)	0.0190 (7)	0.0178 (7)	−0.0037 (6)	0.0057 (5)	−0.0021 (5)
C14	0.0210 (7)	0.0280 (8)	0.0188 (7)	−0.0011 (6)	0.0045 (6)	−0.0012 (6)
C15	0.0238 (8)	0.0304 (9)	0.0195 (7)	−0.0080 (7)	−0.0032 (6)	0.0028 (6)
C16	0.0289 (9)	0.0513 (12)	0.0226 (8)	−0.0084 (9)	0.0036 (7)	0.0073 (8)
C17	0.0205 (7)	0.0174 (7)	0.0221 (7)	0.0028 (6)	−0.0005 (6)	−0.0031 (6)
C18	0.0266 (8)	0.0196 (8)	0.0349 (9)	−0.0029 (6)	0.0016 (7)	−0.0030 (6)

O1—C13	1.4289 (17)	C7—C8	1.373 (2)
O1—C9	1.4425 (17)	C7—H7	0.9500
O2—C15	1.203 (2)	C8—C9	1.503 (2)
O3—C15	1.353 (2)	C9—C10	1.507 (2)
O3—C14	1.4435 (18)	C9—H9	1.0000
O4—C17	1.204 (2)	C10—C11	1.326 (2)
O5—C17	1.3494 (19)	C10—H10	0.9500
O5—C12	1.4537 (18)	C11—C12	1.501 (2)
N1—C7	1.3482 (19)	C11—H11	0.9500
N1—N2	1.3591 (18)	C12—C13	1.524 (2)
N1—C1	1.4320 (19)	C12—H12	1.0000
N2—N3	1.3113 (19)	C13—C14	1.511 (2)
N3—C8	1.3617 (19)	C13—H13	1.0000
C1—C6	1.384 (2)	C14—H14A	0.9900
C1—C2	1.387 (2)	C14—H14B	0.9900
C2—C3	1.387 (2)	C15—C16	1.489 (2)
C2—H2	0.9500	C16—H16A	0.9800
C3—C4	1.389 (3)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C4—C5	1.384 (3)	C17—C18	1.494 (2)
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.392 (2)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—H6	0.9500
C13—O1—C9	112.08 (11)	C9—C10—H10	119.1
C15—O3—C14	117.93 (13)	C10—C11—C12	121.97 (14)
C17—O5—C12	117.77 (12)	C10—C11—H11	119.0
C7—N1—N2	110.90 (12)	C12—C11—H11	119.0
C7—N1—C1	129.40 (13)	O5—C12—C11	107.19 (12)
N2—N1—C1	119.55 (12)	O5—C12—C13	108.46 (12)
N3—N2—N1	106.72 (12)	C11—C12—C13	109.44 (12)
N2—N3—C8	109.38 (13)	O5—C12—H12	110.6
C6—C1—C2	121.36 (14)	C11—C12—H12	110.6
C6—C1—N1	119.64 (14)	C13—C12—H12	110.6
C2—C1—N1	118.96 (14)	O1—C13—C14	107.51 (12)
C3—C2—C1	119.13 (15)	O1—C13—C12	107.63 (12)
C3—C2—H2	120.4	C14—C13—C12	115.09 (13)
C1—C2—H2	120.4	O1—C13—H13	108.8
C2—C3—C4	120.28 (15)	C14—C13—H13	108.8
C2—C3—H3	119.9	C12—C13—H13	108.8
C4—C3—H3	119.9	O3—C14—C13	109.89 (12)
C5—C4—C3	119.84 (15)	O3—C14—H14A	109.7
C5—C4—H4	120.1	C13—C14—H14A	109.7
C3—C4—H4	120.1	O3—C14—H14B	109.7
C4—C5—C6	120.51 (16)	C13—C14—H14B	109.7
C4—C5—H5	119.7	H14A—C14—H14B	108.2
C6—C5—H5	119.7	O2—C15—O3	123.73 (16)
C1—C6—C5	118.85 (15)	O2—C15—C16	125.44 (17)
C1—C6—H6	120.6	O3—C15—C16	110.83 (16)
C5—C6—H6	120.6	C15—C16—H16A	109.5
N1—C7—C8	104.66 (13)	C15—C16—H16B	109.5
N1—C7—H7	127.7	H16A—C16—H16B	109.5
C8—C7—H7	127.7	C15—C16—H16C	109.5
N3—C8—C7	108.34 (13)	H16A—C16—H16C	109.5
N3—C8—C9	122.66 (13)	H16B—C16—H16C	109.5
C7—C8—C9	128.96 (14)	O4—C17—O5	123.09 (14)
O1—C9—C8	110.58 (12)	O4—C17—C18	125.26 (14)
O1—C9—C10	111.38 (12)	O5—C17—C18	111.64 (14)
C8—C9—C10	112.47 (12)	C17—C18—H18A	109.5
O1—C9—H9	107.4	C17—C18—H18B	109.5
C8—C9—H9	107.4	H18A—C18—H18B	109.5
C10—C9—H9	107.4	C17—C18—H18C	109.5
C11—C10—C9	121.71 (14)	H18A—C18—H18C	109.5
C11—C10—H10	119.1	H18B—C18—H18C	109.5
C7—N1—N2—N3	−0.21 (17)	C7—C8—C9—O1	60.2 (2)
C1—N1—N2—N3	−176.19 (13)	N3—C8—C9—C10	7.9 (2)
N1—N2—N3—C8	−0.02 (16)	C7—C8—C9—C10	−174.61 (14)
C7—N1—C1—C6	−21.1 (2)	O1—C9—C10—C11	9.9 (2)
N2—N1—C1—C6	154.08 (15)	C8—C9—C10—C11	−114.87 (16)
C7—N1—C1—C2	161.09 (15)	C9—C10—C11—C12	3.5 (2)
N2—N1—C1—C2	−23.8 (2)	C17—O5—C12—C11	124.32 (14)
C6—C1—C2—C3	−2.0 (2)	C17—O5—C12—C13	−117.60 (14)
N1—C1—C2—C3	175.82 (14)	C10—C11—C12—O5	135.30 (15)
C1—C2—C3—C4	1.4 (2)	C10—C11—C12—C13	17.9 (2)
C2—C3—C4—C5	−0.1 (3)	C9—O1—C13—C14	−165.40 (12)
C3—C4—C5—C6	−0.7 (3)	C9—O1—C13—C12	70.07 (14)
C2—C1—C6—C5	1.2 (2)	O5—C12—C13—O1	−169.07 (11)
N1—C1—C6—C5	−176.58 (15)	C11—C12—C13—O1	−52.44 (15)
C4—C5—C6—C1	0.2 (3)	O5—C12—C13—C14	71.10 (15)
N2—N1—C7—C8	0.34 (16)	C11—C12—C13—C14	−172.27 (13)
C1—N1—C7—C8	175.81 (14)	C15—O3—C14—C13	117.54 (15)
N2—N3—C8—C7	0.23 (17)	O1—C13—C14—O3	−63.44 (16)
N2—N3—C8—C9	178.14 (13)	C12—C13—C14—O3	56.45 (17)
N1—C7—C8—N3	−0.34 (16)	C14—O3—C15—O2	3.6 (2)
N1—C7—C8—C9	−178.08 (14)	C14—O3—C15—C16	−176.58 (13)
C13—O1—C9—C8	78.46 (14)	C12—O5—C17—O4	3.6 (2)
C13—O1—C9—C10	−47.37 (15)	C12—O5—C17—C18	−177.05 (14)
N3—C8—C9—O1	−117.28 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4i	0.95	2.29	3.2207 (19)	167
C9—H9···Cg1ii	1.00	2.68	3.5362 (16)	144
C16—H16a···N3iii	0.98	2.62	3.463 (2)	145
C16—H16b···O2ii	0.98	2.59	3.570 (2)	177
C18—H18a···O1iv	0.98	2.54	3.516 (2)	174
C18—H18c···O4v	0.98	2.45	3.400 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O4i	0.95	2.29	3.2207 (19)	167
C9—H9⋯Cg1ii	1.00	2.68	3.5362 (16)	144
C16—H16a⋯N3iii	0.98	2.62	3.463 (2)	145
C16—H16b⋯O2ii	0.98	2.59	3.570 (2)	177
C18—H18a⋯O1iv	0.98	2.54	3.516 (2)	174
C18—H18c⋯O4v	0.98	2.45	3.400 (2)	164

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .